Masland ran for re-election to the Windsor-Orange 2 District in 2010. He and [[Margaret Cheney]] (D) both won re-election in the general election on [[Vermont House of Representatives elections, 2010|November 2, 2010]].<ref>[http://vermont-elections.org/elections1/2010GEStateSenateRepandCountyListandVoteTotals11.15.pdf Vermont Elections Division - 2010 Election Results]</ref>

Masland ran for re-election to the Windsor-Orange 2 District in 2010. He and [[Margaret Cheney]] (D) both won re-election in the general election on [[Vermont House of Representatives elections, 2010|November 2, 2010]].<ref>[http://vermont-elections.org/elections1/2010GEStateSenateRepandCountyListandVoteTotals11.15.pdf Vermont Elections Division - 2010 Election Results]</ref>

Masland served on the Select Board of Thetford from 1986 to 1999. He joined the Vermont State House of Representatives in 1999. He has served in that position since, representing the Windsor-Orange-2 District.

Masland was the Director of Upper Valley School-to-Work from 1996 to 2000. He also worked as Regional Coordinator for the Upper Valley Commerce and Education Alliance during this time. He has been self-employed as the owner of a Builder/General Contractor Business since 1974. He has also owned Masland Construction since 1975. Masland has worked for the Upper Valley Commerce and Education Alliance as Director since 2000. From 2001 to the present, he has been the self-employed owner of a Workforce Development Consultant Business. He has also been the Coordinator of the Upper Valley Workforce Investment Board since 2002. He has worked as the Site Supervisor of the Upper Valley Habitat for Humanity since 2006 as well.